Use of pyrrolopyrimidines for controlling pests

ABSTRACT

Pyrrolopyrimidines of formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5  and A have the meanings given in the description, and their acid-addition salts and metal salt complexes are very highly suitable for combatting vegetable and animal pests. 
     Novel pyrrolopyrimidines of formula (Ia) in which R 6 , R 7 , R 8 , R 9 , R 10  and Z have the meanings given in the description, and their acid-addition salts and metal salt complexes, and a process for their production. ##STR1##

TECHNICAL FIELD OF THE INVENTION

The present invention relates to the use of Pyrrolopyrimidines, some ofwhich are known, for controlling harmful plants and animals.Additionally, the invention also relates to novel pyrrolopyrimidines andto a process for their preparation.

BACKGROUND OF THE INVENTION

It is already known that certain pyrrolopyrimidines have pharmacologicalproperties (cf. J. Med. Chem. 1995, (38), 3884-3888). However, afungicidal or insecticidal activity of these compounds has hitherto notbeen described.

It has now been found that the pyrrolopyrimidines of the formula##STR2## in which R¹ represents halogen, alkoxy or halogenoalkoxy,

R² represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy,alkylthio, halogenoalkoxy or halogenoalkylthio,

R³ represents optionally substituted aryl or represents optionallysubstituted heteroaryl,

R⁴ and R⁵ independently of one another each represent hydrogen, halogenor alkyl and

A represents alkanediyl or represents an alkanedlyl which is interruptedby one or more heteroatoms or heteroatom groups, where the heteroatomsare not adjacent if a plurality of heteroatoms is present,

and also their acid addition salts and metal salt complexes are highlysuitable for controlling harmful plants and animals.

Surprisingly, the substances which can be used according to theinvention have considerably better activity against harmful plants andanimals than the constitutionally most similar compounds of the priorart having the same direction of action.

The formula (I) provides a general definition of the pyrrolopyrimidineswhich can be used according to the invention.

R¹ preferably represents fluorine, chlorine, bromine, iodine, alkoxyhaving 1 to 4 carbon atoms or halogenoalkoxy having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms.

R² preferably represents hydrogen, fluorine, chlorine, bromine, iodine,alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 identical or different halogen atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms.

R³ preferably represents aryl having 6 to 10 carbon atoms or representsheteroaryl having 3 to 12 ring members, where these radicals may in eachcase be mono- to pentasubstituted by identical or different substituentsselected from the group consisting of halogen, cyano, nitro, formyl,carbamoyl, thiocarbamoyl;

alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 5 carbon atoms;

trialkylsilyl having 1 to 5 carbon atoms in each alkyl moiety;

alkenyl or alkenyloxy having in each case 2 to 4 carbon atoms;

halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinylor halogenoalkylsulphonyl having in each case 1 to 4 carbon atoms and 1to 5 identical or different halogen atoms;

in each case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 4 carbon atoms and 1 to 5identical or different halogen atoms;

alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxirninoalkyl, alkoximinoalkyl or cyanirmino(alkoxy)alkyl having ineach case 1 to 4 carbon atoms in the individual alkyl moieties;

and in each case doubly attached dioxyalkylene having 1 or 2 carbonatoms or alkylene having 3 or 4 carbon atoms with which is optionallymono- to tetrasubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms and halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

a radical of the formula ##STR3## and also phenyl or phenoxy, wherethese two radicals may for their part be mono- to pentasubstituted byidentical or different substituents selected from the group consistingof halogen, cyano, nitro, carbamoyl, thiocarbamoyl, alkyl having 1 to 5carbon atoms, phenyl;

halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms;

straight-chain or branched alkoxy or alkylthio having 1 to 4 carbonatoms;

and straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms;

and in each case doubly attached dioxyalkylene having 1 or 2 carbonatoms or alkylene having 3 to 4 carbon atoms which is optionally mono-to tetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkyl having 1 to 4 carbon atoms andhalogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms.

R⁴ and R⁵ independently of one another each preferably representhydrogen, fluorine, chlorine, bromine, iodine or alkyl having 1 to 4carbon atoms.

A preferably represents alkanediyl having 1 to 8 carbon atoms orrepresents alkanediyl having 1 to 8 chain members, where 1 or 2(non-adjacent) chain members are replaced by oxygen, sulphur and/or SO₂and where a termninal oxygen or sulphur atom or an SO₂ group is in eachcase attached to a radical R³.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, are in each casestraight-chain or branched, including in combination with heteroatoms,such as an alkoxy, alkylthio or alkylamino.

R¹ particularly preferably represents fluorine, chlorine, bromine,methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy.

R² particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio or trifluoroethylthio.

R³ particularly preferably represents phenyl, furyl, thienyl, thiazolyl,thiadiazolyl, pyridyl or pyrimidyl, where these radicals may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, nitro, formyl,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- orneo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl), methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsuiphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, trimethylsilyl, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl,methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethylor cyanoimino(methoxy)methyl,

in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

cyclopropyl, cyclopentyl or cyclohexyl,

a radical of the formula ##STR4## and also phenyl or phenoxy, wherethese two radicals may for their part be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3-or 4-(2-methylbutyl), methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio and phenyl,

and in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl.

R⁴ and R⁵ independently of one another each particularly preferablyrepresent hydrogen, methyl, fluorine, chlorine, bromine or iodine.

A particularly preferably represents the groups --CH₂ -- ##STR5## CH₂--CH₂ --, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-,2,2- or 2,3-butylene or 1,1-, 1,2- or 1,3-(2-methyl-propylene), --(CH₂)₂--O--, --(CH₂)₂ --S--, --(CH₂)₃ --O--, --(CH₂)₃ --S--, --(CH₂)₄ --O--,--(CH₂)₄ --S--, --(CH₂)₅ --O--, --(CH₂)₅ --S--, --(CH₂)₆ --O--, --(CH₂)₆--S--or --(CH₂)₂ --SO₂ --, where in each case the oxygen or the sulphuratom or the SO₂ group of the abovementioned groups is attached to theradical R³.

Compounds which are preferably to be used according to the inventionalso include addition products of acids and those pyrrolopyrimidines ofthe formula (I) in which R¹, R², R³, R⁴, R⁵ and A each have thosemeanings which have been mentioned as being preferred for theseradicals.

The acids which can be added preferably include hydrohalic acids, suchas, for example, hydrochloric acid and hydrobromic acid, in particularhydrochloric acid, furthermore phosphoric acid, sulphuric acid, nitricacid, mono- and bifunctional carboxylic acids and hydroxycarboxylicacids, such as, for example, acetic acid, maleic acid, succinic acid,furmaric acid, tartaric acid, citric acid, salicylic acid, sorbic acidand lactic acid, and also sulphonic acids, such as, for example,p-toluenesulphonic acid, 1,5-naphthalinedisulphonic acid, saccharine andthiosaccharine.

Preferred compounds according to the invention are additionally theaddition products of salts of metals of main groups II to IV andsub-groups I and II and also IV to VIII of the Periodic Table of theElements and those pyrrolopyrimidines of the formula (I) in which R¹,R², R³, R⁴, R⁵ and A each have those meanings which have been mentionedas being preferred for these radicals.

Particular preference in this context is given to salts of copper, zinc,manganese, magnesium, tin, iron and nickel. Suitable anions of thesesalts are those which are derived from those acids which lead tophysiologically acceptable addition products.

Particularly preferred acids of this kind in this context are thehydrohalic acids, such as, for example, hydrochloric acid andhydrobromic acid, furthermore phosphoric acid, nitric acid and sulphuricacid.

Some of the pyrrolopyrimidines which can be used according to theinvention are known (cf. J. Med. Chem. 1995, (38), 3884-3888).

The pyrrolopyrimidines of the formula ##STR6## in which a) R⁶ representsfluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy,

R⁷ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio or trifluoroethylthio,

R⁸ represents phenyl, furyl, thienyl, thiazolyl, thiadiazolyl, pyridylor pyrimidyl, where these radicals may be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3-or 4-(2-methylbutyl), methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl,trimethylsilyl, acetyl, propionyl, acetyloxy, methoxycarbonyl,ethoxycarbonyl, butoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl, ethoximinoethyl orcyanoimino(methoxy)methyl,

in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl) which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

cyclopropyl, cyclopentyl or cyclohexyl,

a radical of the formula ##STR7## and also phenyl or phenoxy, wherethese two radicals may for their part be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3-or 4-(2-methylbutyl), methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio and phenyl,

and in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane- 1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl.

R⁹ and R¹⁰ independently of one another each represent hydrogen, methyl,fluorine, chlorine, bromine or iodine,

Z represents the groups --CH₂ --CH₂ --, 1,1-, 1,2-, 1,3- or2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2-or 1,3-(2-methylpropylene), --(CH₂)₂ --O--, --(CH₂)₂ --S--, --(CH₂)₃--O--, --(CH₂)₃ --S--, --(CH₂)₄ --O--, --(CH₂)₄ --S--, --(CH₂)₅ --O--,--(CH₂)₅ --S--, --(CH₂)₆ --O--, --(CH₂)₆ --S--or --(CH₂)₂ --SO₂ --,where in each case the oxygen or the sulphur atom or the SO₂ group ofthe abovementioned groups is attached to the radical R⁸,

or

b) R⁶ represents fluorine, chlorine, bromine, methoxy, ethoxy, n- ori-propoxy, difluoromethoxy, trifluoromethoxy, difluoromethoxy,trifluoromethoxy,

R⁷ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio or trifluoroethylthio,

R⁸ represents phenyl which is mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of bromine,cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl),methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, tifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl, trifluoromethylsulphonyl, trimethylsilyl,acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,butoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxirninomethyl, hydroxiniinoethyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl, ethoximinoethyl orcyanoimino(methoxy)methyl,

respectively doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

cyclopropyl, cyclopentyl or cyclohexyl,

and also phenyl or phenoxy, where these two radicals may for their partbe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl),methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio andphenyl,

and in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

or

R⁸ represents thienyl or furyl, where these radials are mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, nitro, fornyl,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- orneo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl), methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, trimethylsilyl, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl,methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl .or cyanoimino(methoxy)methyl,

in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

cyclopropyl, cyclopentyl or cyclohexyl,

and also phenyl or phenoxy, where these two radicals may for their partbe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl),methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio andphenyl,

and in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is mono- to tetrasubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl,

or

R⁸ represents thiazolyl, thiadiazolyl, pyridyl or pyrimridyl where theseradicals may be mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3- or 4-(2-methylbutyl),methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl, trifluoromethylsulphonyl, trimethylsilyl,acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,butoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl, ethoximinoethyl orcyanoimino(methoxy)methyl,

in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl) which is optionally mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

cyclopropyl, cyclopentyl or cyclohexyl,

a radical of the formula ##STR8## and also phenyl or phenoxy, wherethese two radicals may for their part be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3- or neo-pentyl, 1-, 2-, 3-or 4-(2-methylbutyl), methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio and phenyl,

and in each case doubly attached ethylenedioxy, methylenedioxy ortrimethylene (propane-1,3-diyl), which is optionally mono totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, methyl, trifluoromethyl,ethyl, n- or i-propyl,

R⁹ and R¹⁰ independently of one another each represent hydrogen, methyl,fluorine, chlorine, bromine or iodine and

Z represents the groups --CH₂ -- or ##STR9## or c) R⁶ representsfluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy, difluoromethoxy, trifluoromethoxy,

R⁷ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio or trifluoroethylthio,

R⁸ represents phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and methoxy,

R⁹ represents hydrogen, fluorine, chlorine, bronine or iodine,

R¹⁰ represents hydrogen, fluorine, chlorine, bromine or iodine and

Z represents the groups --CH₂ -- or ##STR10## but where R⁹ and R¹⁰ donot simultaneously represent hydrogen if R⁸ represents phenyl or2-fluoro-phenyl and Z represents --CH₂ --,

and their acid addition salts and metal salt complexes are novel.

The pyrrolopyrimidines of the formula (Ia) and their acid addition saltsand metal salt complexes can be prepared by reacting pyrrolopyrimidinederivatives of the formula ##STR11## in which R⁶, R⁷, R⁹, and R¹⁰ areeach as defined above

with compounds of the formula

    X--Z--R.sup.8                                              (III),

in which

Z and R⁸ are each as defined above and

X represents halogen, alkylsulphonyl or arylsulphonyl,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent, and subsequently adding, if appropriate, anacid or a metal salt.

The other compounds of the formula (I) can be prepared in the samemanner.

A large number of the compounds which can be used according to theinvention contain asynrmnetrically substituted carbon atoms. Thesecompounds may be present in the form of stereoisomers or as mixturesthereof. The invention relates both to the individual isomers and totheir mixtures. Using 4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine andbenzyl chloride as starting materials, the course of the processaccording to the invention can be illustrated by the following equation:##STR12##

The formula (II) provides a general definition of the pyrrolopyrimidinederivatives required as starting materials for carrying out the processaccording to the invention. In this formula (II), R⁶, R⁷, R⁹ and R¹⁰each have those meanings which have already been mentioned in connectionwith the description of the compounds of the formula (Ia) according tothe invention as being preferred or as being particularly preferred forR⁶, R⁷, R⁹ and R¹⁰.

The starting materials of the formula (II) are known or can be preparedby known processes (cf. Chem.Ber., (1942), 75, 755; J.Org.Chem., (1961)26, 3809; Chem.Ber. (1979) 112, 3432; Chem.Ber. (1979) 112, 799; LiebigsAnn.Chem. (1984), 273-282; Liebigs Ann.Chem. (1984) 722-733; LiebigsAnn.Chem. (1985) 312-320 J.Med.Chem. (1985) 28, 1461-1467).

The formula (III) provides a general definition of the substancesrequired as reaction components for carrying out the process accordingto the invention. In this formula, R⁸ and Z each have those meaningswhich have already been mentioned in connection with the description ofthe compounds of the formula (Ia) according to the invention. Xpreferably represents chlorine, bromine, methylsulphonyl or4-tolylsulphonyl.

The compounds of the formula (III) are known or can be prepared by knownprocesses.

Suitable acid binders for carrying out the process according to theinvention are all customary inorganic or organic bases. Preference isgiven to using alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates,such as sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodiumacetate, potassium acetate, calcium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate or sodium bicarbonate, furthermoreammonium compounds, such as ammonium hydroxide, ammonium acetate orammonium carbonate, and also tertiary amines, such as trimethylamine,triethylamine or tributylaamine, N,N-dimethylaniline,N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out the process according to theinvention are all customary inert organic solvents. Preference is givento using aliphatic, alicyclic or aromatic hydrocarbons, such aspetroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisol; ketones, such as acetone, butanone,methyl-isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters such asmethyl acetate or ethyl acetate; sulphoxides, such as dimethylsulphoxide; sulphones, such as sulpholane.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between -20° C. and +180°C., preferably at temperatures between 20° C. and 130° C.

The process according to the invention is usually carried out underatmospheric pressure. However, it is also possible to carry out theprocess according to the invention under elevated or reduced pressure.

When carrying out the process according to the invention, generally 0.5to 10 mol, preferably 0.8 to 3 mol, of a compound of the formula (III)are employed per mole of pyrrolopyrimidine derivative of the formula(II). Work-up is carried out by customary methods. In general, thereaction mixture is concentrated under reduced pressure, the residuethat remains is taken up in an organic solvent which is only sparinglymiscible with water, and the resulting solution is washed with waterand, after drying, concentrated under reduced pressure. The product thatis obtained can, if appropriate, be freed of any impurities that maystill be present using customary methods, for example chromatography orrecrystallization.

The pyrrolopyrimidines of the formula (Ia) can be converted into acidaddition salts or metal salt complexes.

For preparing acid addition salts of the compounds of the formula (Ia),preference is given to using those acids which have already beenmentioned as being preferred acids in connection with the description ofthe acid addition salts which can be used according to the invention.

The acid addition salts of the compounds of the formula (Ia) can beobtained in a simple manner by customary salt formation methods, forexample by dissolving a compound of the formula (Ia) in a suitable inertsolvent and addition of the acid, for example hydrochloric acid, and canbe purified in a known manner, for example by filtering off, isolationand, if appropriate, by washing with an inert organic solvent.

For preparing metal salt complexes of the compounds of the formula (Ia),preference is given to using those salts of metals which have alreadybeen mentioned in connection with the description of the metal saltcomplexes which can be used according to the invention as preferredmetal salts.

The metal salt complexes of the compounds of the formula (Ia) can beobtained in a simple manner by customary processes, for example bydissolving the metal salt in alcohol, for example ethanol, and adding itto compounds of the formula (Ia). Metal salt complexes can be purifiedin the known manner, for example by filtering off, isolation and, ifappropriate, by recrystallization.

The active compounds which can be used according to the invention have apotent microbicidal activity and can be employed for controllingundesirable microorganisms, such as fungi and bacteria, in cropprotection and in the protection of materials.

Fungicides can be employed in crop protection for controllingPlasmo-diophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceacand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as Xanthomonas campestris pv. oryzae;

Pseudomonas species, such as Pseudomonas syringae pv. lachrymans;

Erwinia species, such as Erwinia amylovora;

Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli orPseudoperonospora cubensis;

Plasmopara species, such as Plasmopara viticola;

Bremnia species, such as Bremia lactucae,

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Podosphaera species, such as for example Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea (conidiaform: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as Cochliobolus sativus (conidia form:Drechslera, syn: Helminthosporium);

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Sclerotinia species, such as Sclerotinia sclerotiorum;

Tilletia species, such as Tilletia caries;

Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea;

Septoria species, such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

Alternaria species, such as for example Alternaria brassicae;

Pseudocercosporella species, such as Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds which can be used according to the invention can beemployed here particularly successfully for controlling cereal diseases,such as against Leptospaeria species, diseases in viticulture, food andvegetable growing, such as against Venturia, Podosphaera and Plasmoparaspecies.

Other cereal diseases, such as Erysiphe, Septoria, Pyrenophora orCochliobolus species, and also rice diseases, such as Pyriculariaspecies, are also controlled very successfully.

In the protection of materials, the substances which can be usedaccording to the invention can be employed for protecting industrialmaterials against attack and destruction by undesirable microorganisms.

In the present context, the term industrial materials refers tonon-living materials which have been prepared for use in industry.Examples are industrial materials which are to be protected by activecompounds according to the invention against microbial alteration ordestruction, adhesives, sizes, paper and card, textiles, leather, wood,coating compositions and plastic articles, cooling lubricants and othermaterials which can be infested or decomposed by microorganisms. In thecontext of the materials to be protected mention may also be made ofparts of production plants, for example cooling water circuits, whichmay be adversely affected by reproduction of microorganisms. Preferredindustrial materials of which mention may be made in the context of thepresent invention are adhesives, sizes, papers and cards, leather, wood,coating compositions, cooling lubricants and heat transfer fluids,particularly preferably wood.

By way of example, mention may be made of microorganisms of thefollowing genera:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

The active compounds which can be used according to the invention arewell tolerated by plants and have favourable homeotherm toxicity, andthey can additionally be employed for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forests, in horticulture, in the protection of storedproducts and of materials and also in the hygiene sector and in theveterinary field. The substances are active against normally sensitiveand resistant species and also against pests in all or specific stagesof development. The abovementioned animal pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus. Fromthe order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Spodoptera litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include Pratylenchus spp., Radopholussirmilis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heteroderaspp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorusspp., Xiphinema spp. and Trichodorus spp.

The substances which can be used according to the invention can beemployed particularly successfully for controlling plant-damaging mites,such as against the greenhouse red spider mite (Tetranychus urticae), orfor controlling plant-damaging insects, such as against the caterpillarsof the diamond-back moth (Plutella maculipennis), the larvae of themustard beetle (Phaedon cochleariae) and also the green rice leaf hopper(Nephotettix cincticeps).

The substances which can be used according to the invention are not onlyactive against plant, hygiene and stored-product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites)such as hard ticks, soft ticks, mange mites, Trombiidae, flies (stingingand sucking), parasitic fly larvae, lice, hair lice, bird lice andfleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the sub-orders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the sub-orders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and supella spp.

From the sub-class of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otabiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knernidocoptes spp., Cytodites spp. and Larninosioptes spp.

The active compounds which can be used according to the invention arealso suitable for controlling arthropods which attack agriculturallivestock, such as, for example, cattle, sheep, goats, horses, pigs,donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,honeybees, other domestic animals such as, for example dogs, cats, cagebirds, aquarium fish, and so-called experimental animals, such as, forexample, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, it is intended to reduce deaths and decreasing performance(in meat, milk, wool, hides, eggs, honey and the like), so that moreeconomical and simpler animal keeping is possible by using the activecompounds according to the invention.

Furthermore, it has been found that the compounds which can be usedaccording to the invention have a potent insecticidal action againstinsects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis; Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec., Dinoderus minutus

Dermapterans, such as Sirexjuvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticuliternes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials, such as, preferably, synthetic materials,glues, sizes, paper and board, leather, wood and timber products, andpaint.

The materials to be very particularly preferably protected againstattack by insects are wood and timber products.

Wood and timber products which can be protected by compounds accordingto the invention are to be understood as meaning, for example,construction timber, wooden beams, railway sleepers, bridge components,jetties, wooden vehicles, boxes, pallets, containers, telephone poles,wood lagging, windows and doors made of wood, plywood, particle board,joiner's articles, or wood products which, quite generally, are used inthe construction of houses or in joinery.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. In the case of the use of water as an extender, organicsolvents can, for example, also be used as auxiliary solvents.Essentially, the following are suitable as liquid solvents: aromaticssuch as xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water. Liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at standardtemperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, or else butane, propane,nitrogen and carbon dioxide. Suitable solid carriers are: for exampleground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly disperse silica, alumina and silicates. Suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks. Suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds which can be used according to the invention can beused as such or in their formulations also mixed with known fungicides,bactericides, acaricides, nematicides or insecticides in order thus, forexample, to widen the spectrum of action or to prevent development ofresistance. In many cases, synergistic effects are achieved, i.e. theactivity of the mixture exceeds the activity of the individualcomponents.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticdiin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimnidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

2',6'-dibromo-2-methyl4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamnide, 2-aminobutane,

2-phenylphenol (OPP),

8-hydroxyquinoline sulphate,

cis-1-(4-chlorophenyl)-2-(1 H-1,2,4-triazol-1-yl)-cycloheptanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetrarnethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

1-[1-[2-[(2 ,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-irnidazole,

bis-(1-methylethyl)-3-methyl4-[(3-methylbenzoyl)oxy]-2,5-thiophenedicarboxylate,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone-O-(phenylmethyl)-oxime,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]- H-1,2,4-triazole,methanetetrathiol-sodium salt,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N'-methoxy-methanirnidamide,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylenel-1H-1,2,4-triazole-1-ethanol,

1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl-1H-pyrrol-2,5-dione,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonarnide, methylN-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,spiro[2H]-1-benzopyrane-2,1'(3'H)-isobenzofuran]-3'-one,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,potassium bicarbonate,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[(diiodomethyl)-sulphonyl]4-methyl-benzene,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden4-yl)-3-pyridinecarboxamide

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

3,5-dichloro-N-fcyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methylcyclopropanecarboxamide,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamnycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalarn, copper sulphate and othercopper preparations.

Insecticides/Acaricides/Nematicides:

abamnectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamnethrin, armitraz, averrnec tin, AZ 60541, azadirachtin, azinphosA, azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap,CGA 157 419, CGA 184699, chloethocarb, chiorethoxyfos, chlorfenvinphos,chiorfluazuron, chiormephos, chiorpyrifos, chiorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cyperrnethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron,diazinon, dichlofenthion, dichiorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disuiphoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamniphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucytlirinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mevinphos, mesulphenphos, metaldehyde, methacrifos,metharnidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, MI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirinricarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulphotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

It is also possible to admix other known active compounds, such asherbicides or fertilizers and growth regulators.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by pouring, spraying,atonizing, broadcasting, dusting, foaming, brushing-on and the like. Itis further possible to apply the active compounds by the ultra-lowvolume method or to inject the preparation of active compound, or theactive compound itself, into the soil. The seeds of the plants can alsobe treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range: They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to50g, preferably 0.01 to 10 g, are generally required per kilogram ofseed.

In the treatment of the soil, active compound concentrations of from0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight,are required at the site of action.

The compositions which are used for protecting industrial materialscontain the active compounds generally in an amount of from 1 to 95%,preferably of from 10 to 75%.

The use concentrations of the active compounds which are to be usedaccording to the invention depend on the nature and the occurrence ofthe microorganisms to be controlled and also on the composition of thematerial to be protected. The optimum amount to be employed can bedetermined by test series. Generally, the. use concentrations are in therange of from 0.001 to 5% by weight, preferably from 0.05 to 1.0% byweight, based on the material to be protected.

The effectiveness and activity the spectrum of the active compoundswhich are to be used according to the invention in the protection ofmaterials, or of the compositions, concentrates or quite generallyformulations which can be prepared therefrom, can be increased byadding, if appropriate, further compounds having antimicrobial action,fungicides, bactericides, herbicides, insecticides or other activecompounds to widen the activity spectrum or to obtain particulareffects, such as, for example, the additional protection againstinsects. These mixtures may have a broader activity spectrum than thecompounds which can be used according to the invention.

When used against animal pests, too, the substances which can be usedaccording to the invention, in commercially available formulations andalso in the use forms prepared from these formulations, can be presentas a mixture with synergists. Synergists are compounds which enhance theeffectiveness of the active compounds, without it being necessary forthe synergist which is added to be active itself.

The content of active compound in the use forms prepared from thecommercially available formulations can vary within wide ranges. Theconcentration of active compound in the use forms can be from 0.0000001to 95% by weight of active compound, preferably between 0.0001 and 1% byweight.

Application is carried out in a manner which is appropriate for the useforms.

In the veterinary sector, the active compounds which can be usedaccording to the invention are used in a known manner by enteraladministration, for example in the form of tablets, capsules, drinks,drenches, granules, pastes, boluses, the feed-through method,suppositories, by parenteral administration, such as, for example, bymeans of injections (intramuscular, subcutaneous, intravenous,intraperitonal and the like), implants, by nasal application, by dermaladministration, for example in the form of dipping or bathing, spraying,pouring-on and spotting-on, washing, dusting, and with the aid of shapedarticles which comprise active compound, such as collars, eartags, tailmarks, limb bands, halters, marking devices and the like.

When administered to livestock, poultry, domestic animals and the like,the active compounds can be used as formulations (for example powders,emulsions, flowables) which comprise the active compounds in an amountof from 1 to 80% by weight, either directly or after dilution by afactor of 100 to 10,000, or they may be used in the form of a chemicalbath.

If the substances which are to be used according to the invention areemployed as insecticides for protecting wood and timber products, theconcentrates or the ready-to-use formulations generally comprise theactive compounds in concentrations of between 0.0001 and 95% by weight,preferably between 0.001 and 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and the occurrence of the insects and on the medium. For use, theoptimum amount to be employed can in each case be determined by testseries. In general, however, it is sufficient to employ from 0.001 to20% by weight, preferably from 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

A particularly effective protection of wood with the aid of activecompounds according to the invention is achieved by using large-scaleindustrial impregnation processes, for example vacuum, double-vacuum orpressure processes.

The ready-to-use compositions may comprise further insecticides and/orfungicides. Particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and also fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and the use of active compounds which are to be usedaccording to the invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1 ##STR13##

1.3 g (0.01 mol) of benzyl chloride are added to a suspension of 1.7 g(0.01 mol) of 4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine and 2.1 g(0.015 mol) of potassium carbonate, and the mixture is heated at refluxfor 18 hours. The reaction mixture is allowed to cool to roomtemperature and then concentrated under reduced pressure. The residuethat remains is taken up in 200 ml of dichloromethane. The resultingmixture is washed with 100 ml of water and then dried over sodiumsulphate and concentrated under reduced pressure. This gives 2.0 g (78%of theory) of 7-benzyl-4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine inthe form of an oil.

¹ H-NMR: δ=2.77 (s, 3H); 5.42 (s, 2H); 6.54 (d, 1H); 7.08 (d, 1H) ppm.

The substances listed in Table 1 are also prepared following theprocedures given in Example 1 and in the description.

                                      TABLE 1                                     __________________________________________________________________________                                                                (I)                                                                             #STR14##           -                                                                          Example                                                                         No. R.sup.1 R.sup.2 A R.sup.3 R.sup.4 R.sup.5 Physical data                 __________________________________________________________________________     2   --Cl  --CH.sub.3                                                                         --CH.sub.2 --                                                                          4-chlorophenyl      H  H  mp.: 87°  C.                                                             3 --Cl --CH.sub.3                                                           --CH.sub.2 -- 3-chlorop                                                       henyl H H mp.:                                                                83°  C.                                                                  4 --Cl --CH.sub.3                                                           --CH.sub.2 --CH.sub.2                                                         -- Phenyl H H NMR:                                                            2.76(s, 3H); 3.12(t,                                                                  2H); 4.47(t,                                                          2H)*                          5 --Cl --CH.sub.3 --CH.sub.2 -- 4-t-butylphenyl H H NMR: 1.29(s, 9H);                                                         2.78(s,                             3H); 5.39(s, 2H)*                                                       6 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --O Phenyl H H mp.: 70°                                                         C.                             **)                                                                         7 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 -- 4-t-butylphenyl H H NMR:                                                           1.30(s, 9H); 2.75                                                                    (s, 3H)*                                                                 8 --Cl --CH.sub.3                                                           --CH.sub.2 --CH.sub.2                                                         --O-- 2,6-dichloropheny                                                       l H H mp.: 121°                                                         C.                             **)                                                                         9 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 -- Nitrophenyl H H mp.:                                                               144°  C.                                                                10 --Cl --S--CH.sub.3                                                        --CH.sub.2 -- Phenyl H                                                        H mp.: 54°  C.                                                          11 --Cl --S--CH.sub.3                                                        --CH.sub.2 -- 4-chlorop                                                       henyl H H mp.:                                                                104°  C.                                                                12 --Cl --S--CH.sub.3                                                        --CH.sub.2 -- 3-chlorop                                                       henyl H H mp.:                                                                92°  C.                                                                 13 --Cl --S--CH.sub.3                                                        --CH.sub.2 -- 4-t-butyl                                                       phenyl H H NMR:                                                               1.29(s, 9H); 2.63(s,                                                                  3H); 5.34(s,                                                          2H)*                         14 --Cl --CH.sub.3 --CH.sub.2 -- 4-t-butoxycarbonyl- H H mp.: 127.degree                                                       .  C.                            phenyl                                                                    15 --Cl --S--CH.sub.3 --CH.sub.2 -- 4-t-butoxycarbonyl- H H mp.:                                                               110°  C.                                                                    phenyl                  16 --Cl --H --CH.sub.2 -- 4-chlorophenyl H H mp.: 123°  C.                                                               17 --Cl --H --CH.sub.2                                                        -- Phenyl H H mp.:                                                           63°  C.                                                                 18 --Cl --H --CH.sub.2                                                        -- 3-chlorophenyl H H                                                        mp.: 96°  C.                                                            19 --Cl --H --CH.sub.2                                                        -- 4-t-butyl-phenyl H                                                        H mp.: 89°  C.                                                          20 --Cl --H --CH.sub.2                                                        -- 4-t-butoxycarbonyl-                                                        H H mp.: 104°                                                         C.                               phenyl                                                                    21 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 4-bromophenyl H H mp.:                                                          121°  C.                                                                   **)                      22 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 2-methoxyphenyl H H mp.:                                                        93°  C.                                                                    **)                      25 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 -- Phenyl H H mp.: 49°                                                           C.                           26 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 -- 3-trifluormethylphenyl H H                                                           mp.: 58°  C.                                                            27 --O--CH.sub.3                                                             --CH.sub.3 --CH.sub.2                                                         -- 3-chlorophenyl H H                                                         mp.: 51°  C.                                                            28 --O--CH.sub.3                                                             --CH.sub.3 --CH.sub.2                                                         -- 4-chlorophenyl H H                                                         mp.: 97°  C.                                                            29 --Cl --H --CH.sub.2                                                        -- 4-trimethylsilylphe                                                       nyl H H NMR: 0.00(s,                                                          9H); 5.21(s,                        2H); 8.43(s, 1H)*                                                      30 --Cl --CH.sub.3 --CH.sub.2 -- 4-trimethylsilylphenyl H H NMR:                                                               0.00(s, 9H); 2.53(s,                                                                  3H); 5.17(s,                                                          2H)*                         31 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 -- 4-trimethylsilylphenyl H H                                                           NMR: 0.00(s, 9H);                                                             2.44(s,                             3H); 3.86(s, 3H);                                                             5.15(s, 2H)*                                                            - 32 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              H H mp.: 115°                                                         C.                           - 33 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H mp.: 120°                                                         C.                           - 34 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              H H mp.: 113°                                                         C.                           - 35 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H   NMR: 2.66(s,                                                          3H); 4.11(s,  3H);                                                            5.38(s, 2H)*                  - 36 --Cl --H --CH.sub.2 --                                                                                                     H H mp.: 122°                                                         C.                           - 37 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 4-chlorophenyl H H                                                           mp.: 122°  C.                                                           38 --Cl --CH.sub.3                                                           --CH.sub.2 --CH.sub.2                                                         --O-- 4-methoxyphenyl                                                         H H mp.: 86°                                                           C.                              **)                                                                        39 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 2,4-dichlorophenyl H H                                                          mp.: 114°  C.                                                              **)                       - 40 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              H H   NMR: 0.68(t,                                                          3H);  1.28(s,  3H);                                                           1.42(s, 3H);  1.62(q,                                                         2H);  2.75(s, 3H)*                                                              - 41 --O--CH.sub.3                                                          --CH.sub.3 --CH.sub.2                                                         --CH.sub.2 --O--                                                              4-chlorophenyl H H                                                            mp.: 79°  C.                                                               **)                      42 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 4-methoxyphenyl                                                        H H mp.: 85°                                                           C.                              **)                                                                        43 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --CH.sub.2 --O-- 2,4-dichlorophen                                                       yl H H mp.: 90°                                                         C.                             **)                                                                         - 44 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H   NMR: 2.66(s,                                                          3H); 4.09(s,  3H);                                                            5.36(s, 2H)*                  - 45 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H   NMR: 2.66(s,                                                          3H); 4.10(s,  3H);                                                            5.32(s, 2H)*                  - 46 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H   NMR: 2.65(s,                                                          3H); 4.08(s,  3H);                                                            5.38(s, 2H)*                  - 47 --O--CH.sub.3 --CH.sub.3 --CH.sub.2 --                                                                                     H H   NMR: 2.65(s,                                                          3H); 4.10(s,  3H);                                                            5.37(s, 2H)*                  - 48 --Cl --CH.sub.3 --(CH.sub.2).sub.6 --O-- 2-chloro-4- H H NMR:                                                            2.63(s, 3H); 3.72                                                                 **) methoxyphenyl                                                          (s, 3H)*                    49 --Cl --CH.sub.3 --(CH.sub.2).sub.6 --O-- 2.5-dimethylphenyl H H NMR:                                                        2.05(s, 3H); 2.24(s,                                                              **)    3H);                                                               2.63(s, 3H)*                  - 50 --Cl H                                                                                                                     #STR25##                                                                      H H   HPLC***): Rf =                                                         889  UV: .sub.max =                                                          226 nm                        - 51 --Cl H                                                                                                                     #STR27##                                                                      H H   HPLC***): Rf =                                                         990  UV: .sub.max =                                                          224 nm                        - 52 --Cl H --CH.sub.2 --                                                                                                       H H mp. 96°                                                          C.                            - 53 --Cl --CH.sub.3                                                                                                            #STR30##                                                                      --Cl H HPLC***): Rf                                                         =  1073  UV: .sub.max                                                         =  232 nm                     - 54 --Cl --CH.sub.3                                                                                                            #STR32##                                                                      --Cl H HPLC***): Rf                                                         =  1158  UV: .sub.max                                                         =  232 nm                     - 55 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              --Cl H mp. 129.degree                                                       .  C.                         - 56 --Cl --CH.sub.3                                                                                                            #STR35##                                                                      H H   HPLC***): Rf =                                                         951  UV: .sub.max =                                                          228 nm                        - 57 --Cl --CH.sub.3 --                                                                                                         #STR37##                                                                      H H   HPLC***): Rf =                                                         1053  UV: .sub.max =                                                         226 nm                        - 58 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              H H mp.: 90°                                                         C.                            - 59 --Cl --CH.sub.3 --CH.sub.2 --CH.sub.2 --  SO.sub.2 --  **)                                                                     HPLC***): Rf =                                                          770  UV: .sub.max =                                                           226 nm                        - 60 --Cl --H                                                                                                                   4-chlorophenyl --H                                                          --H HPLC***): Rf =                                                            978                           - 61 --Cl --H                                                                                                                   4-fluorophenyl --H                                                          --H HPLC***): Rf =                                                            895                           - 62 --Cl --H                                                                                                                   2,6-dichlorophenyl                                                          --H --H HPLC***): Rf =                                                         1040                         - 63 --Cl --H --CH.sub.2 --                                                                                                     --H --H HPLC***): Rf                                                        =  709                        - 64 --Cl --CH.sub.3                                                                                                            4-chlorophenyl --H                                                          --H HPLC***): Rf =                                                            1045                          - 65 --Cl --CH.sub.3                                                                                                            4-fluorophenyl --H                                                          --H HPLC***): Rf =                                                            957                           - 66 --Cl --CH.sub.3                                                                                                            2,6-dichlorophenyl                                                          --H --H HPLC***): Rf =                                                         1138                         - 67 --Cl --H --CH.sub.2 --                                                                                                     --H --H HPLC***): Rf                                                        =  915                        - 68 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              --H --H HPLC***): Rf                                                        =  1057                       - 69 --Cl --CH.sub.3 --CH.sub.2 --                                                                                              --H --H HPLC***): Rf                                                        =  758                     __________________________________________________________________________     *)The .sup.1 HNMR spectra were recorded in deuterochloroform (CDCl) or        hexadeuterodimethyl sulphoxide (DMSOd.sub.6) using tetramethylsilane (TMS     as internal standard. Stated is the chemical shift as δ  value in       ppm.                                                                          **)The atom labelled ** is in each case attached to the radical R.sup.3.      ***)In the HPLC analysis, the retention index (Rf) was determined based o     the 2alkanones (C3 to C16) on a C18 reversed phase HPLC using the gradien     system phosphoric acid (0.1% strength)/acetonitrile.                     

USE EXAMPLES Example A

Plasmopara Test (grape vines)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatingis dried on, the plants are inoculated with an aqueous spore suspensionof plasmopara viticola and then remain in an incubation cabin at 20° C.and 100% relative atmospheric humidity for 1 day. The plants aresubsequently placed in a greenhouse at 21° C. and approximately 90%atmospheric humidity for 5 days. The plants are then moistened andplaced in [lacuna] incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                  TABLE A                                                         ______________________________________                                        Plasmopara test (grape vine)/protective                                                                   Efficacyin % at a con-                                centration of active                                                        Active compound compound in the spray                                         According to the invention: liquor of 100 ppm                               ______________________________________                                                                 90 R51##                                                (2)                                                                           -                                                                                                   85 R52##                                               (22)                                                                           -                                                                                                   83 R53##                                               (24)                                                                        ______________________________________                                    

Example B

Podosphaera Test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are inoculated with an aqueous spore suspensionof the causative organism of apple mildew, Podosphaera leucotricha.

The plants are then placed in a greenhouse at 23° C. and a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                  TABLE B                                                         ______________________________________                                        Podosphaera test (apple)/protective                                                                       Efficacyin % at a con-                                centration of active                                                        Active compound compound in the spray                                         According to the invention: liquor of 100 ppm                               ______________________________________                                                                 100 54##                                               (2)                                                                         ______________________________________                                    

Example C

Venturia Test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are inoculated with an aqueous conidiasuspension of the causative organism of apple scab, Venturia inaequalisand then remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 20° C. and a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                  TABLE C                                                         ______________________________________                                        Venturia test (apple)/protective                                                                          Efficacyin % at a con-                                centration of active                                                        Active compound compound in the spray                                         According to the invention: liquor of 100 ppm                               ______________________________________                                                                 91 R55##                                               (2)                                                                         ______________________________________                                    

Example D

Leptosphaeria Nodorum Test (wheat)/protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are sprayed with aspore suspension of Leptosphaeria nodorum. The plants remain in anincubation cabin at 20° C. and 100% relative atmospheric humidity for 48hours.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

                  TABLE D                                                         ______________________________________                                        Leptosphaeria nodorum test (wheat)/protective                                                            Application                                           rate of active                                                               Active compound compound Efficacy                                             According to the invention: in g/ha in %                                    ______________________________________                                                                           250 100                                      (2)                                                                         ______________________________________                                    

Example E

Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with mustard beetle larvae (Phaedon cochleariae) while theleaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE E                                     __________________________________________________________________________    (plant-damaging insects)                                                        Phaedon larvae test                                                                                Concentration of                                         Active compound active compound in                                            According to the invention: the spray liquor in % Kill in % after 7         __________________________________________________________________________                                     d                                                                               0.1 100                                      (2)                                                                            -                                                                                                             0.1 100                                      (3)                                                                            -                                                                                                             0.1 100                                      (6)                                                                            -                                                                                                             0.1 100                                      (26)                                                                           -                                                                                                             0.1 100                                      (41)                                                                           -                                                                                                             0.1 100                                      (42)                                                                           -                                                                                                             0.1 100                                      (47)                                                                        __________________________________________________________________________

    __________________________________________________________________________                                         0.1 100                                  (41)                                                                             -                                                                           ##STR65##                      0.1 100                                          - (42)                                                                        -                                                                                                          ##S 0.1 100                                      - (47)                                                                     __________________________________________________________________________

Example F

Plutella Test

Solvent: 7 parts by weight of dimethylfomamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamond-backed moth (Plutellaxylostella) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE F                                     __________________________________________________________________________    (plant-damaging insects)                                                        Plutella test                                                                                      Concentration of                                         Active compound active compound in                                            According to the invention: the spray liquor in % Kill in % after 7         __________________________________________________________________________                                     d                                                                               0.1 100                                      (2)                                                                            -                                                                                                             0.1 100                                      (3)                                                                            -                                                                                                             0.1 100                                      (17)                                                                        __________________________________________________________________________

Example G

Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the green rice leaf hopper (Nephotettixcincticepts) while the seedlings are still moist.

After the desired period of time, the kill in % is determined. 100%means that all leaf hoppers have been killed; 0% means that none of theleaf hoppers have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE G                                     __________________________________________________________________________    (plant-damaging insects)                                                        Nephotettix test                                                                                     Concentration of                                       Active compound active compound in                                            According to the invention: the spray liquor in % Kill in % after 6         __________________________________________________________________________                                       d                                                                               0.1 100                                    (2)                                                                            -                                                                                                               0.1 100                                    (8)                                                                            -                                                                                                               0.1 100                                    (25)                                                                           -                                                                                                               0.1 100                                    (26)                                                                           -                                                                                                               0.1 100                                    (30)                                                                           -                                                                                                               0.1 100                                    (31)                                                                        __________________________________________________________________________

    ______________________________________                                                                            0.1 100                                   (26)                                                                             -                                                                           ##STR77##                  0.1 100                                              - (30)                                                                        -                                                                                                      ##STR7 0.1 100                                       - (31)                                                                     ______________________________________                                    

Example H

Tetranychus Test (OP resistant/dip treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

After the desired period of time, the effect in % in determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

                                      TABLE H                                     __________________________________________________________________________    (plant-damaging insects)                                                        Tetranychus test (OP-resistant/dip treatment)                                                       Concentration of                                        Active compound active compound in                                            According to the invention: the spray liquor in % Kill in % after 7         __________________________________________________________________________                                      d                                                                               0.1 100                                     (1)                                                                            -                                                                                                              0.1 100                                     (5)                                                                            -                                                                                                              0.1 100                                     (7)                                                                            -                                                                                                              0.1 100                                     (17)                                                                           -                                                                                                              0.1 100                                     (26)                                                                           -                                                                                                              0.1 100                                     (30)                                                                           -                                                                                                              0.1 100                                     (31)                                                                        __________________________________________________________________________

    ______________________________________                                                                            0.1 100                                   (17)                                                                             -                                                                           ##STR87##                  0.1 100                                              - (26)                                                                        -                                                                                                      ##STR8 0.1 100                                       - (30)                                                                     ______________________________________                                    

    ______________________________________                                                                            0.1 100                                   (31)                                                                          ______________________________________                                    

What is claimed is:
 1. A method for controlling undesired microorganismsand animal pests, comprising the step of applying an effective amount ofa pyrrolopyrimidine of the formula (I) ##STR90## wherein R¹ representsfluorine, chlorine, bromine, iodine, alkoxy having 1 to 4 carbon atomsor halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms,R² represents hydrogen, fluorine, chlorine,bromine, iodine, alkyl having 1 to 4 carbon atoms, halogenoalkyl having1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms or halogenoalkylthio having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms, R³ represents arylhaving 6 to 10 carbon atoms or represents heteroaryl having 3 to 12 ringmembers, wherein each is unsubstituted or mono- to pentasubstituted byidentical or different substituents selected from the group consistingof halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl, alkyl,alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case1 to 5 carbon atoms,trialkylsilyl having 1 to 5 carbon atoms in eachalkyl moiety, alkenyl or alkenyloxy having in each case 2 to 4 carbonatoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio,halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1to 4 carbon atoms and 1 to 5 identical or different halogen atoms, ineach case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 4 carbon atoms and 1 to 5identical or different halogen atoms, alkylcarbonyl, alkylcarbonyloxy,alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl, alkoximinoalkyl orcyanimino(alkoxy)alkyl having in each case 1 to 4 carbon atoms in theindividual alkyl moieties; and in each case doubly attacheddioxyalkylene having 1 or 2 carbon atoms or alkylene having 3 or 4carbon atoms with which is unsubstituted or mono- to tetrasubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1or 2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 6 carbon atoms, a radical of the formula##STR91## and phenyl or phenoxy, where these two radicals areunsubstituted or mono- to pentasubstituted by identical or differentsubstituents selected from the group consisting of halogen, cyano,nitro, carbamoyl, thiocarbamoyl, alkyl having 1 to 5 carbon atoms,phenyl,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms, straight-chain or branched alkoxy or alkylthiohaving 1 to 4 carbon atoms, and straight-chain or branchedhalogenoalkoxy or halogenoalkylthio having 1 to 4 carbon atoms and 1 to5 identical or different halogen atoms, and in each case doubly attacheddioxyalkylene having 1 or 2 carbon atoms or alkylene having 3 to 4carbon atoms which is unsubstituted or mono- to tetrasubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1to 2 carbon atoms and 1 to 5 identical or different halogen atoms, R⁴and R⁵ independently of one another each represent hydrogen, fluorine,chlorine, bromine, iodine or alkyl having 1 to 4 carbon atoms, and Arepresents alkanediyl having 1 to 8 carbon atoms or representsalkanediyl having 1 to 8 chain members, where 1 or 2 non-adjacent chainmembers are replaced by a heteroatom or heteroatom group selected fromthe group consisting of oxygen, sulphur and SO₂ and wherein a terminaloxygen or sulphur atom or an SO₂ group is in each case attached to aradical R³.